We have a higher end rental in this area (albeit unfurnished) and I have seen my property management company advertise several high end furnished homes on their site (5-7k/month range), with some listed as short term winter rentals.  

I have several spots for them throughout the twin cities.

@Brandon Swartwood Instead of giving something to a contractor, have several contractors come to the property and ask for their SOW.

With a buy and hold philosophy you are accomplishing several things to give you the "out" you'll  want to quit comfortably one day.1.

Meet several brokers and Agents and let them know what you are looking for and build y'alls relationship. 

For example, my city has several small communities within a 30 minutes drive, but my city has lots of affordable housing and you can drive 10 minutes to work.

I, however did not have nearly enough to purchase several properties outright; I would have needed financing.

I have PM’s in several states and they all outsource lawn care, maintenance, etc and bill me for it in addition to their fee.

Only downside was I had already spent several days replacing trim boards before it happened. 

After reading several articles from an affiliate website (I don't think I'm supposed to mention affiliates by name??)